Quynh: This synthesis has some good strategies, and I am glad that you are using some of the reactions presented in class. There is really only one major problem that I see. The carboxylic acid will not be compatable with the basic conditions of the acetylide reacton and the coupling. My suggestion is to start with 8-bromo octanol and protect the alcohol part There are a number of reagents that will work One the comes to mind is THP or tetrahydropyranyl which is made from the alcohol and dihydropyranwith catalytic amount of acid. It can be removed with trifllouroacetic acid and water. Many reagents that will oxidize the alcohol to an acid will not touch tha double or triple bonds. Event he Jones oxidation will work if you are careful to keep the temperature around 0C. If you can not find 8-bromo octanol at Aldrich, I know a trick to make it from 1,8-octanediol. I will try to mention it in class on Tuesday. If I forget please remind me. Bruce Bondurant
Place syntheses below.
FIRST DRAFT OF SYNTHESIS:
Quynh:
This synthesis has some good strategies, and I am glad that you are using some of the reactions presented in class. There is really only one major problem that I see. The carboxylic acid will not be compatable with the basic conditions of the acetylide reacton and the coupling. My suggestion is to start with 8-bromo octanol and protect the alcohol part There are a number of reagents that will work One the comes to mind is THP or tetrahydropyranyl
Bruce Bondurant
RETROSYNTHESIS:
FINAL DRAFT OF SYNTHESIS:
This is good. The reterosynthesis is exactly what I am looking for.
Bruce Bondurant